People First, And Then Profits Follow with Dean Mathews

28 Jan 2026 · 42 min
Episode

28 Jan 2026 · 42 min

0:00

This content was created by Bill Gallagher. This content was uploaded by Bill Gallagher. This is a podcast episode titled "People First, And Then Profits Follow with Dean Mathews" (PODCAST) created/recorded 2025-10-01. It’s an interview-style conversation hosted by Bill Gallagher (Scaling coach, Scaling Up Business podcast) with guest Dean Mathews, founder of OnTheClock. They discuss Dean’s 2004 bootstrapped SaaS time-tracking, scheduling and payroll business (now ~$5M revenue, ~22 employees, ~16,000 customers), early product/marketing choices, hiring and delegation, building company culture, technical re-architecture, integrations with payroll ecosystems (ADP, Gusto, QuickBooks), moving toward built-in payroll and a sales-led motion, and goals to reach ~1M monthly active users. The episode includes practical lessons for founders and leadership/personal reflections; producers Anna and Wanda are also mentioned.

Questions this episode answers

2004 (idea late 2003; product live ~3–4 months later in 2004).

About $5 million.

22 (author anticipates 23–24 soon).

About 16,000 companies.

Around 150,000 (guest later states closer to 200,000 monthly users).

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